Organic Colorant Complexes from Reactive Dyes and Articles Containing the Same

Abstract

An organic colorant complex with the following general structure: AB n (DE) m T x Q y wherein A is an organic chromophore; B is an electrophilic reactive group covalently bonded to A directly or through a linking group; D is a nucleophilic linking group covalently bonding B and E, selected from the group consisting of NR, O, S, and 4-oxyanilino (—HN-Ph-O—); wherein R is selected from the group consisting of H, alkyl, aryl, and E; E is an organic alkyl and aryl group or an end group; T is an ionic group covalently linked to A; Q is an organic cation, bonded to the organic chromophore A through ionic interaction with T; n, m, x, and y are independent integers from 1 to 10.

We claim: 
     
         1 . An organic colorant complex with the following general structure (I):
   AB n (DE) m T x Q y   (I)
   wherein   A is an organic chromophore selected from an azo, phthalocyanine or anthraquinone chromophore group;   B is an electrophilic reactive group selected from monochlorotriazine, monofluorotriazine, dichlorotriazine, sulfatoethyl sulfone, vinyl sulfone, 2,3-dichloroquinoxaline, and 2,4-difluor-5-chloropyrimidine groups and is covalently bonded to A directly or through a linking group;   D is a nucleophilic linking group covalently bonding B and E, selected from NR, O, S, and 4-oxyanilino (—HN-Ph-O—); wherein R is H, alkyl, aryl or E;   E is an organic moiety or an end group;   T is a cationic quaternary ammonium group covalently linked to A;   Q is a counterion, bonded to the organic chromophore through ionic interaction with T; and   n, m, x, and y each independently are integers of 1-10.   
     
     
         2 . A method for preparing the organic colorant complex of  claim 1 , comprising the steps of
 (a) reacting, under basic conditions, a reactive dye of the formula AB n T x M x  with a nucleophile organic compound DE to form a compound of the formula AB n (DE) m T x M x ,   (b) reacting the compound AB n (DE) m T x M x  with an organic cationic compound, Q + Z −  wherein Q is a cation and Z is an anion to form the organic colorant complex of the formula AB n (DE) m T x Q y  and   (c) purifying the colorant complex to remove inorganic salts.   or   (a′) covalently bonding reactive dye AB to a nucleophile DE by heating an aqueous or organic composition of nucleophile and the dye to a temperature of at least 30° C. at a pH of the reaction composition which avoids protonating amine if present in the reaction mixture   (b′) reacting the formed anionic colorant from (a′) with a cationic compound T x Q y  to form the desired colorant complex, and   (c′) purifying the colorant complex to remove inorganic salts.   wherein   A is an organic chromophore selected from an azo, phthalocyanine or anthraquinone chromophore group;   B is an electrophilic reactive group selected from monochlorotriazine, monofluorotriazine, dichlorotriazine, sulfatoethyl sulfone, vinyl sulfone, 2,3-dichloroquinoxaline, and 2,4-difluor-5-chloropyrimidine groups and is covalently bonded to A directly or through a linking group;   D is an atom with lone electron pair for nucleophilic reaction,   E is an organic moiety covalently linked to D,   T is a cationic quaternary ammonium group covalently linked to A;   M is a metal counter cation;   m is an integer of 1-10;   n is an integer of 1-10; and   x is an integer of 1-10.   
     
     
         3 . The use of the organic colorant complex of  claim 1  for coloring media selected from polymers, aqueous solutions, thermoplastic composites, thermosets, waxes, ink formulations, plastics, detergents, soaps and crayons.